US1629894A - Process for the manufacture of 2:3-aminonaphthoic acid - Google Patents

Process for the manufacture of 2:3-aminonaphthoic acid Download PDF

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US1629894A
US1629894A US97768A US9776826A US1629894A US 1629894 A US1629894 A US 1629894A US 97768 A US97768 A US 97768A US 9776826 A US9776826 A US 9776826A US 1629894 A US1629894 A US 1629894A
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acid
manufacture
parts
ammonia
aminonaphthoic
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US97768A
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Tobler Richard
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OF CHEMICAL INDUSTRY OF BASLE
SOCIETY OF CHEMICAL INDUSTRY OF BASLE
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OF CHEMICAL INDUSTRY OF BASLE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
    • C07C309/47—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton having at least one of the sulfo groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system

Definitions

  • amlnat on may be much simplified, improving further the yields of the dry process, by heating the 2:3-hydroxynaphthoic acid in a closedyessel w'th an excess of aqueous ammoma 1n the pfiesence of a salt of a bivalent metal which salt is soluble in water in presence of an ex- ..cess of ammonia, such as zinc chloride or 'calcium chloride.
  • a process for the manufacture of 2:3 aminonaphthoic acid consisting in heating 2:3-hydroxynaphthoic acid in a closed vessel with an excess of aqueous ammonia in the presence of a salt of a bivalent metal which salt is soluble in water in presence of an excess of ammonia.
  • a process for the manufacture of 2:3- aminonaphthoic acid consisting in heating 2 :3-hydroxynaphthoic acid in a closed vessel with an excess of ammonia in presence of zinc chloride.

Description

Patented May 24, 1927.
UNITED STATES PATENT OFFICE.
RICHARD TOIBLER, OF BASEL, SWITZERLAND, AS SIGNOR TO SOCIETY OI CHEMICAL INDUSTRY OF BASLE, OF BASEL, SWITZERLAND.
PROCESS FOR THE MANUFACTURE OF 2:3-AMIN0NAP HTHOIC ACID.
No Drawing. Application filed latch 28, 1926, Serial No. 97,768, and in Switzerland April 8, 1925.
Until lately the 2:3-aminonaphthoic acid corresponding with the formula DOE has been made by heating the 2:3-hydroxynaphthoic acid with aqueous ammonia under increased pressure. This process leads to bad yields, with formation of considerable quantities of B-naphthol and ,B-naphthylamine as by-products (c.f. Berichte der deutschen Chemischen Gesellschaft No. 28, 3096). a
Since, it has also been recommended to carry out the amination in a dry process. By this method better yields are obtained (f. Helv. Chimica Acta V 1922 p. 558). The practical realization of the process, however, ofl'ers certain difficulties as to the device employed, hard lumps being very easily formed.
It has now been found that the amlnat on may be much simplified, improving further the yields of the dry process, by heating the 2:3-hydroxynaphthoic acid in a closedyessel w'th an excess of aqueous ammoma 1n the pfiesence of a salt of a bivalent metal which salt is soluble in water in presence of an ex- ..cess of ammonia, such as zinc chloride or 'calcium chloride.
E wample 1.
250 parts of zinc chloride are dissolved in 300 parts of water, the solution is then mtroduced into an autoclave provided with a stirrer and treated with 500 parts of 2:3-hydroxynaphthoic acid. The autoclave is then closed and 120 to 140 parts of gaseous ammonia are introduced into it. The whole is heated for 24 hours at 220-230 (temperature of the oil bath) which operation produces a pressure of 12 to 20 atm. The reaction mixture forms a rather thick yellow mass which is boiled with 4000 parts of water and 1400 parts of concentrated hydrochloric acid whereby almost complete solution occurs. The hot solution is filtered,
the filtrate treated with 12004500 parts of common salt and allowed to cool whereby the 2:3-aminonaphthoic acid hydrochloride filtrateby addition of acid, or the solution may be worked up directly. Yield above 00% of the theory.
Example 2.
250 parts of zinc chloride are dissolved in 531 parts of an aqueous solution of ammonia of 24.7% strength. This solution is intro-' duced into an autoclave together with 500 parts of 2:3-hydroxynaphthoic acid. The autoclave is closed and heated, while stirring, for about 36 hours at 220-230 (temperature of the oil bath) and at a pressure of 15-20 atm. The reaction mixture forms a dilute yellow mass which is worked up as, indicated in the previous example.
What I claim is:
1. A process for the manufacture of 2:3 aminonaphthoic acid, consisting in heating 2:3-hydroxynaphthoic acid in a closed vessel with an excess of aqueous ammonia in the presence of a salt of a bivalent metal which salt is soluble in water in presence of an excess of ammonia.
2. A process for the manufacture of 2:3- aminonaphthoic acid, consisting in heating 2:3-hydroxynaphthoic acid in a closed vessel with an excess of ammonia in presence of a zinc salt. 4
3. A process for the manufacture of 2:3- aminonaphthoic acid, consisting in heating 2 :3-hydroxynaphthoic acid in a closed vessel with an excess of ammonia in presence of zinc chloride.
In Witness whereof I have hereunto signed my name this 13th day of March 1926.
RICHARD TOSBLER.
US97768A 1925-04-08 1926-03-26 Process for the manufacture of 2:3-aminonaphthoic acid Expired - Lifetime US1629894A (en)

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